“I am a divorced woman who was married for 25 years. For the past 13 months, I have been dating a man who is wonderful in many ways but still enjoys partying on a nightly basis. He gets high on weed a couple of evenings a week, and also downs 24 to 48 ounces of wine as part of his typical routine. I have spoken to him a number of times about this because it seems like excessive behavior for a 54 year old man, but he insists that he’s just having fun, that he has never missed work or gotten a DUI over it, and that his health is fine. He says, “I’m straight all day. Why should I have to be that way at night?” My instincts are telling me to run away even though I care deeply for him. Am I being too much of an alarmist?”
A woman in her 20s from the Bay Area asks, “Have you ever seen people successfully use upcoming OKCupid dates as a negotiating tactic to get someone in real life to date them? I know it sounds like a terrible idea, but maybe if done right it could move someone from the friend zone into the dating zone on a semi-subconscious level by sparking their interest and making them realize it’s a now or never type opportunity?”
A divorced straight woman in her early 40s wrote, “I love my ex husband, and I’m so sad that we didn’t work out. I would get back together with him now, but he says he’s done. I’m still confused as to why that didn’t work out. We both love each other so much. I have been dating a lot for two years now, and I have yet to find a guy that I really connect with. I wonder if I’m doomed to be single my whole life now that I’ve lost my ex husband. Do you have any advice to give me other than ‘soldier on and I’ll eventually meet someone’?” We do, of course, have some advice, and the writer included a link to her OKCupid profile, which figures into our response.
“I disclose my HSV2 (genital herpes) status in my dating profile. I was getting many messages before putting the HSV2 on there, and I’m still getting many messages, only now at least I have a sense of freedom and honesty. I hope it will help me filter the boys from the men, though I’m not entirely sure it’s helping. Do you think it is wise to be as honest as I am?”
A married woman in an open relationship struggles with how to handle the most important man in her life who isn’t her husband: he’s her coworker, best friend, and her husband’s friend. They started hanging out and making out two years before when he was in an abusive relationship, but they never had sex at his insistence. Even though he has since broken up with his girlfriend, they make out but haven’t had sex. They’ve both declared their love for each other, but it causes her pain when he makes out with her but refuses to consummate the relationship. Even worse, he blames her for the situation when he pulls away, only to resume flirting and wooing her. Her friends say that he is either “playing me, really messed up from his bad relationship, or just a drunk. I would love your take on a) his inconsistent behavior and b) whether I should try to have a calm conversation with him about our friendship, or just go with the flow.”
“I’m currently fooling around and flirting with a few guys. I’m newly single and having a lot of fun. I sometimes wonder if monogamous relationships are just not for me. I tried it and I get bored really easily. I like getting a lot of attention and I get frustrated with just one guy. I feel like there’s no way one guy can give me all the attention I crave. Is this just a phase because I’m young and selfish or is this just me?”
A woman in her early twenties from the New York suburbs wrote in the heat of the moment that, “I was about to text this guy that I have been having casual sex with for the last three months, several times a week, and tell him I need to stop. We met online. He is 10 years older than I am, and I think I may be developing feelings for him, although I try and act cold and detached. I have a lot of other specifics, but I don’t want to bombard you. It was just super weird that I came across you just now.”
“I was in a FWB situation for almost 8 months with this guy. We never went on real dates and mostly met at his drum studio or apartment, talked, and had sex. For me anyway, it was a rare intellectual connection combined with great chemistry. Sex was great, conversations were great, and time passed so quickly with hi. He was not OK with the polyamorous thing and didn’t want to get emotionally involved but was OK with having sex since it was out in the open. I was OK with simply enjoying the times we had together. So, that was working well until one day he just dropped out in the middle of rescheduling one of our meetups because the schedule that day didn’t work out. Like all of a sudden, gone. To this day I’m just still extremely puzzled by this. I’ve moved on and I’m not mad or anything, but just deeply curious. Like, what the hell happened?”
“Maybe you can give me some tips on how to find a girl to join my boyfriend and me.” So says a Brooklyn woman in a three-and-a-half year relationship that she describes as open. Maybe we know voodoo and spells too. That’s not sarcastic; we just might. Regardless, the hunt for the elusive unicorn is on. In case you don’t know, the unicorn is that rare, magical bisexual woman who will jump into bed with with a couple and help them fulfill their fantasies.
A 26 year-old Brooklyn woman writes, “I love that I’m surrounded by so many smart and ambitious women in New York, but unfortunately that means we’re all in competition for the same six manchildren. The dudes on OKCupid (and maybe NYC?) are flaky as hell, and I’m tired of having a few great dates where things click, and then nothing. I sort of suspect that the only way I’ll end up in a good long-term relationship is if I leave NYC. I’d be very curious if you two think there’s something I could change about my approach or perspective!”
A 41 year-old divorced woman who does not, to our knowledge, tango or live in Paris writes, “I identify as a sex-positive, joyful and mature person who was married for a long time and has recently re-entered the dating scene. I had a hot tryst while on a work trip abroad that unlocked some unknown erotic treasure trove in me. There was nothing this guy could do wrong, and it kind of made me into a desiring machine. Tried as I did to forget and replace this lover, nothing came close to that voltage generated by us. There is no long term potential with that man (we both have kids from previous relationships who we are committed to loving and prioritizing), but the dialog continues at a leisurely pace. Should I just cut this off, stop obsessing about him to clear space for new partners to come into my life, or continue to patiently nourish a situation I felt was so unique and precious? Is there such a thing as an ideal pheromone match?”
A 38 year-old single woman with a kid writes, “Would it be possible to have you take a look at my OKCupid profile and hypothesize why I keep getting guys who are upfront from the beginning that they aren’t looking for a something long-term? They say they’re monogamish, busy, etc. I’m interested in, though not desperate for, a life partner. I also find many of the men who message me are far older than I am and/or from out of state. Neither of those things is particularly interesting to me.”